How to Pitch SideHustle LIVE Internally to Your CMO

How do I get my CMO to approve booking SideHustle LIVE?

Lead with the audience demographics (73% business decision-makers per real data over 5 events), the comparison to traditional alternatives (keynote / panel / DJ all score lower on engagement), and propose a Pilot Experience as the de-risk on-ramp. Most companies test the format with a Pilot Show Sponsorship before scaling.

The story

You watched the sizzle. You saw the testimonials. You're convinced SideHustle LIVE is right for your event. Now you have to sell it to someone who hasn't seen it. Here's the 4-line summary you put in Slack first:

"Found a comedy game show built for founders called SideHustle LIVE. Audience pitches business ideas alongside improv comedians. 100% audience participation, 75-90 min, built for corporate. Used by [orgs in our space]. Want me to set up a 15-min call?"

If the response is curious, send the 1-pager case: Audience that shows up (per our data over 5 events: 70-100 paid attendees, 42% Founder/Owner, 22% Tech/SaaS, 73% confirmed business decision-makers when you combine Founder + Revenue + Product + Operator). Proof: Co-founders Tomer Soran + Darby Rollins, Austin-based, 5 prior shows in Austin + Asheville. Investment range: Pricing scales by partnership tier. Most companies start with a Pilot Experience to test before scaling.

What it means

The three objections you'll hear: (1) Is this actually professional or amateur improv? Cast is 3-4 professional improv performers + host + co-host + 1-2 audience facilitators. Production specs include 5 wired mics, 4 wireless, mixer, PA, audio engineer. (2) Will our audience engage or sit there with arms crossed? Format is structurally designed for participation. By round 2 every table has its own running joke. (3) How does this connect to our brand goals? We custom-craft against your brand. Branded visuals, custom prompts featuring your products, lead capture, networking activation built around your booth.

Try it

• Show your CMO the format: playsidehustle.com
• Catch the live show: Sept 25 at Pershing Hall in Austin. luma.com/playsidehustle
• Book the 15-min call: team@playsidehustle.com